The Americans were in a hurry.
Adam Boehler, a senior U.S. official, wanted Hamas to agree to the release of the last living American Israeli hostage in Gaza so that President Trump could announce his freedom during a speech to Congress.
The two sides were still haggling as Mr. Trump arrived at the Capitol, and they failed to meet the deadline, according to four people familiar with the discussion, leaving the president to make only a passing reference to hostages in Gaza.
Still, the talks, which eschewed decades of entrenched animosity, carried on the next day, demonstrating how eager the two sides were to make a deal.
It all started, and ended, in March. Even though the United States has backed Israel in its campaign in Gaza against Hamas, which launched the Oct. 7, 2023, attack that killed some 1,200 people in Israel, Trump administration officials met with senior Hamas officials in Qatar three times, the four people said. The meetings were a break with longstanding U.S. policy against contact with the armed group, which the United States considers a terrorist organization.
Mr. Trump had made releasing all the hostages a key goal, aiming to show success where the Biden administration struggled. In a meeting with Prime Minister Benjamin Netanyahu this week, though, his comments on hostages were largely overshadowed by tariff talk and Iran diplomacy.
The March talks underscored the Trump administration’s ad hoc approach to diplomacy. But in the face of furious Israeli opposition, Hamas’s hesitation and the Trump administration’s shifting position, an agreement to free the hostage, Edan Alexander, never came together.
This account is based on conversations with six people familiar with the closed-door meetings, all of whom spoke on condition of anonymity to discuss sensitive diplomacy.
The talks were separate from Israel and Hamas’s deadlocked attempts to extend their troubled cease-fire. The first phase of that agreement signed in January had expired without a deal to transition to the second phase, which called for the end of the war and an Israeli withdrawal from Gaza.
Mr. Netanyahu has said the war will not end until Hamas’s military wing and government are dismantled, while Hamas appears willing only to give up control of civilian government but not its arms.
The deadlock left U.S. officials with the impression that it was only a matter of time until Israel resumed its military operations in Gaza, imperiling Mr. Alexander and the release of the bodies of four other Israeli Americans, two people familiar with the matter said. Mr. Boehler believed that Hamas might want to make a gesture to Mr. Trump and that a side deal could build momentum toward serious discussions about Phase 2, they said.
The White House’s National Security Council didn’t respond to a request for comment for this article.
The day of the first meeting, after iftar, the fast-breaking meal during the Muslim holy month of Ramadan, three Hamas officials welcomed Mr. Boehler, a private equity investor who was Mr. Trump’s nominee for special envoy for hostage affairs, and his adviser, a recent graduate of Harvard Business School. They met in a sitting room with a large mural of al-Aqsa Mosque in Jerusalem and a picture of Ismail Haniyeh, the Hamas political chief slain by Israel in July.
Past midnight, the officials reflected on the historic nature of the meeting and ate knafeh, a Middle Eastern pastry, and drank freshly squeezed orange juice. They also discussed the Israeli-Palestinian conflict and the Oct. 7 attack, four people familiar with the conversation said.
The Hamas officials, Taher al-Nono, Basem Naim and Osama Hamdan, made an effort to appeal to their American counterparts’ sensibilities, according to the four people. Mr. al-Nono argued that Hamas was trying to secure freedom for Palestinians — a value he said was cherished by Americans. Some 50,000 people have been killed in the war, according to Gazan health authorities, who don’t distinguish between civilians and combatants, and some protesters in Gaza have called on Hamas to step aside.
Two days after the first meeting, Mr. Boehler returned to talk with Khalil al-Hayya, Hamas’s top negotiator, the four people said. Mr. al-Hayya said Hamas would normally demand the release of 500 Palestinian prisoners from Israeli detention in exchange for a hostage like Mr. Alexander, but in a gesture of good will and to save time, it would ask for only 250, including 100 serving life sentences.
Mr. al-Hayya said that he believed that the United States could push the Israelis into releasing that many people, according to two people familiar with the discussion.
An aide to Mr. al-Hayya and Mr. Naim, a spokesman for Hamas who speaks broadly for the organization, did not respond to detailed requests for comment. A Palestinian official confirmed the broad details of the talks on condition of anonymity.
Later that day, Mr. Boehler offered 100 prisoners serving life sentences and promised to release 150 lower-level prisoners at a future date in exchange for Mr. Alexander, according to three people familiar with the matter.
Israel has roughly 300 prisoners serving life sentences in custody and officials have been wary of giving too many up in exchange for a single hostage.
Mr. Boehler was coming under pressure from Israel over the talks. He received an angry phone call from Ron Dermer, Mr. Netanyahu’s adviser, expressing his frustration that Mr. Boehler had not informed Israel in advance, according to two people familiar with the call. The next day, Axios reported that Mr. Boehler had met with Hamas — a leak that U.S. officials said they believed was orchestrated by Israeli officials to sabotage the talks. Mr. Dermer did not return a request for comment.
The United States often consults with Israel about sensitive national security matters, but Trump administration officials may not have wanted to keep Israeli officials in the loop because Israel had disrupted a previous attempt to meet Hamas leaders.
In that case, immediately after Mr. Trump’s inauguration on Jan. 20, Mr. Boehler traveled to Doha, Qatar, where he hoped to meet with Hamas officials, among other reasons for the trip. But when the Israeli prime minister’s office caught wind of Mr. Boehler’s plans, Israeli officials intervened with the White House, according to two people familiar with the events. The White House called off the meeting.
During the March meetings, Mr. Boehler was in close contact with Steve Witkoff, Mr. Trump’s Middle East envoy, coordinating positions and providing updates, the two people said.
Before the third and final meeting with Hamas, on March 5, U.S. officials no longer felt their offer was possible. They decided that the most they could propose would be 100 prisoners, without a promise that they would be serving life sentences, for Mr. Alexander.
The offer would also include the release of Palestinian women and children for the four bodies of the Israeli American hostages, the resumption of aid deliveries to Gaza and a plan to dispatch Mr. Witkoff to Doha to iron out the details of the exchange and jump-start a conversation about Phase 2, two people familiar with the matter said. Days earlier, Israel had cut off the entry of aid to the territory to pressure Hamas.
The meetings also touched on Hamas’s vision for the future of Gaza. Mr. al-Hayya told his American interlocutors that Hamas was open to a five- to 10-year truce, in which the group would lay down its weapons.
Among other suggestions, Mr. al-Hayya also said that Hamas wanted two leaders of the defunct Texas-based Holy Land Foundation, who were convicted in the United States in 2008 of providing “material support” to the group, to be set free, according to four people familiar with the conversation.
At the end of the last meeting, Mr. Boehler told Mr. al-Hayya that his latest offer was final and might no longer be on the table if Hamas did not accept it by the time his plane took off in a few hours, four people briefed on the matter said. Mr. al-Hayya suggested Hamas would not accept it, even if he wanted the deal himself.
A week later Hamas issued a statement that it was ready to make a deal to release Mr. Alexander and the bodies of the American Israeli hostages. The offer was similar to the one proposed by Mr. Boehler, two people familiar with its contents said.
But it was too little, too late: Mr. Boehler was no longer negotiating directly with the group. When Mr. Witkoff traveled to Doha in mid-March, he demanded Hamas agree to the release of multiple living hostages without guarantees on the end of the war.
Days later, Israel restarted its bombing campaign in Gaza, with Mr. Alexander still in captivity.
Abu Bakr Bashir contributed reporting to this article.
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